By Ariana Bacle
Updated April 09, 2014 at 07:17 PM EDT
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Jeffrey R. Staab/CBS

Late Show With David Letterman

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David Letterman is really bad at prank calling.

Lindsay Lohan went on The Late Show, which airs Wednesday night, and proposed — nay, begged — Letterman to call Oprah on-air. Letterman obliged, calling Oprah and pretending (very unconvincingly) to be Lohan’s secretary until Oprah asked, for the second time, “Who is this?” and he revealed himself.

Oprah has been working with Lohan on OWN docu-series Lindsay, which chronicles the actress’ post-rehab life as she struggles to stay clean, so the first question Letterman asked her was how the starlet’s doing. “I think she’s doing okay,” Oprah said as Lohan started tearing up. “We’re really pleased that she’s making some progress.”

Watch the full clip below:

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Late Show With David Letterman

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